Alkaloids

ALKALOIDS
These are organic products of plant or synthetic origin which are basic in nature and contain
one or more nitrogen atoms, normally of heterocyclic nature, and are physiologically active

Deviations from definition

plant origin: Some alkaloids are also derived from frogs, fungi and animals

Basicity:Some alkaloids are not basic. Eg:Colchicine, Ricinine

Nitrogen: The nitrogen in some alkaloids are not heterocyclic in nature. Eg:Colchicine,
Ephedrine

TRUE ALKALOIDS: Toxic in nature, contain heterocyclic nitrogen, which is derived from
amino acids and are always basic in nature. Present in plants as salts of organic acids. Eg:
Atropine, nicotine, morphine.

PROTO ALKALOIDS or AMINO ALKALOIDS: Simple amines in which nitrogen is not in a

heterocyclic ring. Basic in nature and prepared in plants from amino acids.Eg: Mescaline, N,N-
dimethyl tryptamine, colchicine, ephedrine.

PSEUDO ALKALOIDS: They are not derived from amino acids but contain heterocyclic
nitrogen. They do not show many of the typical characters of alkaloids, but give the standard
qualitative test for alkaloids. Eg: Conessine and caffeine.

Occurrence and distribution

 True alkaloids are of rare occurrencein lower plant
 Dicotyledons, mostly contain the alkaloids than Monocotyledons
 Families rich in alkaloids :Solanaceae, Liliaceae,Rubiaceae,Papaveraceae

properties
 Most alkaloids are well-defined crystalline substances which unite with acids to form
salts. In plants they may exist in the free state, as salts or as N-oxides.

 Free bases of alkaloids are soluble in organic non-polar, immisciblele solvents and are
insoluble in water but the salts of most alkaloids are soluble in water.

 Most of the alkaloids are basic in reaction, due to availability of lone pair of electrons on
nitrogen.Pka values greater than 7.

 Taste: Bitter in taste

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Alkaloids

 Volatile alkaloids : Coniine,Nicotine

 Some alkaloids are coloured in nature eg: Betanidin is red ,berberine is yellowand salts
of sanguinarine are copper red incolour

 It may exist in the form as :

Primary amine(R-NH2) eg: Mescaline
Secondary amine (R2-NH) eg: Ephedrine
Tertiary amine(R3N) eg: Atropine
Quaternary ammonium compounds[R4N+X] eg: Tubocurarine chloride
 Basicity order:R2-NH >R-NH2>R3N ,degree of basicity depends upon the electrostatic
status of nitrogen atom

ISOLATION AND EXTRACTION OFALKALOIDS

METHOD 1 : STAS –OTTO METHOD

Powdered drug containing alkaloidal salts

Defat if necessary Moisten and render alkaline with Na2CO3,

NH3,Ca(OH)
Free alkaloid

Exhaust with organic solvents like chloroform,

Ether
Total extracts

Concentrate & shake with acids like dil.H2SO4

Aq. Acid soln Residual organic Fraction

(alkaloidal salts ) (pigments , fats & very weak bases or
chloroform soluble alkaloid sulphates)

Make alkaline extracts with Organic soln of alkaloid bases

Immiscible solvents
Remove solvent
Residual aqueous fraction
Crude alkaloidal mixture

Purification (by fractional crystallisation, chromatographic separation)

&identification (by analytical techniques such as UV, IR, MNR)
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Alkaloids

METHOD 2:

 The powdered material is extracted with water or aqueous alcohol containing dilute acid.
 Free alkaloids are then precipitated by the addition of sodiurn bicarbonate or ammonia
 Separated by filtration or by extraction with organic solvents.

CHEMICAL TEST FOR ALKALOID

1. MAYER’S TEST (Potassium mercuric iodide solution)

 Gives cream coloured precipitate

2. DRAGENDORFF’S TEST (Potassium bismuth iodide solution)

 Gives reddish brown precipitate

3. WAGNER’S TEST (Iodine-potassium iodide solution)

 Givesreddish brown precipitate

4. HAGER’S TEST(Picric acid solution)

 Gives yellow coloured precipitate

CLASSIFICATION OF ALKALOIDS

A. Biosynthetic Classification
Give significance to the precursor from which the alkaloids are biosynthesized

Examples
(i) Indole alkaloids derived from tryptophan.
(ii) Piperidine alkaloids derived from lysine.

B. Pharmacological Classification: Depends up on the physiological response

Examples
(i) Morphine as Narcotic analgesic
(ii) Quinineas Antimalarial
(iii) Strychnine as Reflex excitability

C. Taxonomic classification :Based on their distribution in variety of Plant Families

Examples
(i) Cannabinaceous Alkaloids: e.g., Cannabis sativa, Linn, (Hemp, Marijuana).

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Alkaloids

(ii) Rubiaceous Alkaloids :e.g., Cinchona Sp. (Quinine)

D. Chemical classification :Mostly accepted classification.Mainly divided into two

A )Heterocyclic alkaloids (True alkaloids)

B )Non-heterocyclic alkaloids

Heterocyclic alkaloids

1. Purine alkaloids
Sl Name Biological source Active Uses
No. constituents
1 Coffee Ripe seed ofCoffea Arabica Trigonelline CNS stimulant
or C. Liberica caffeine
(Fam-Rubiaceae)
2 Cocoa Ripe seed of Theobroma Cocao Theobromine, Diuretic
(Fam-Sterculiaceae) caffiene
3 Tea Leaves and leaf bud of Thea-Sinensis Theobromine, Diuretic,
(Fam-Theaceae) caffiene CNS stimulant
2.Pyridine alkaloids
1 Areca nut Seed of Areca Catechu Arecoline, Respiratory
(Betel nut) (Fam-Palmae) Arecaidine stimulant
2 Lobelia(Indian Aerial part (Stem and leaf)of Lobelia Lobeline, Respiratory
Tobacco / Nicotianaefolia Lobelanidine stimulant
Asthma weed) (Fam-Campanulaceae)
3.Indole alkaloids
Sl Name Biological source Active Uses
No. constituents
1 Ergot Sclerotium of fungus Claviceps Ergometrine, Oxytocic,
(Ergot of rye) Purpurea (Fam-Hypocreaceae). ergotamine treatment of
It is developed in Ovary of Rye migraine
Plant Secale cereal(Fam-Graminae).
2 Nux vomica Ripe seed of Strychnos Nuxvomica Strychnine, CNS stimulant,
(cow Fig) (Fam-Loganiaceae) brucine bitter,stomachic
3 Physostigma Ripe seed of PhysostigmaVenenosum Physostigmine, In glaucoma
(Caabar beans) (Fam-Leguminosae) physovenine
4 Sarpagandha Root of Rauwolfia Serpentina Reserpine, Anti
(Fam-Apocynaceae) rescinnamine Hypertensive
5 Vinca Whole plant of Catharanthus Vincristine and Anti-cancer
Roseus or Vinca Rosea Vinblastine
(Fam- Apocyanaceae)

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Alkaloids

4.Isoquinoline alkaloids

1 Opium Latex or Exudate of unripened Narcotine, Narcotic

fruit(capsule) of Papaver Somniferum papaverine analgesic, In
(Fam-Papaveraceae) diarrhoea
2 Curare Dried extracts of stems &leaves of d-tubocurarine Skeletal muscle
various plants from family chloride Relaxant
Loganiaceae
3 Ipecacunha Root and Rhizome of Cephaelis Emetine, Antiamoebic,
Ipecacuanha or Cephaelis Acuminate cephaeline Emetic,
(Fam-Rubiaceae) Expectorant

5.Tropane alkaloids

1 Belladonna Leaves and flowering tops of Atropa l-hyoscyamine, Anticholinergic,

(Deadly night Belladonna atropine Antispasmodic
shadeleaf) (Fam-Solanaceae)
2 Coca leaves Leaves of Erythroxylon Coca Cocaine, Local
(Fam-Erythroxylaceae) Cinnamyl anaesthetics
cocaine,
3 Datura Leaves and flowering tops Scopolamine, Anticholinergic,
(Angels of Datura Metel var. fastuosa Hyoscyamine, In duodenal
trumpet) (Fam-Solanaceae) atropine ulcers
4 Hyoscyamus Leaves and flowering tops l-hyoscyamine, Anticholinergic,
of Hyoscyamus Niger hyoscine antispasmodic
(Fam-Solanaceae)
5 Stramonium Leaves and flowering tops of l-hyoscyamine, Anticholinergic,
(Thornapple Datura Stramonium hyoscine, Mydriatic,
leaves) (Fam-Solanaceae) atropine motion sickness
6 Duboisia (cork Dried leaves of Duboisia Scopalamine Anticholinergic
tree) mycoporoides,(Fam- Solanaceae)
6.Quinoline alkaloids
1 Camptotheca Stem wood of Camptotheca Camptothecin Anti-cancer
(cancer tree) Acuminate (Fam-Nyssaceae)

2 Cinchona Dried root or Bark of Quinine, Anti malarial,

(Peruvian Cinchona Calisaya ,C. Ledgeriana, Quinidine, Bitter tonic
bark) C. Officinalis, C. Succirubra Cinchonine
(Fam-Rubiaceae) Cinchonidine

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Alkaloids

7.Imidazole alkaloids

1 Pilocarpus Dried leaves of pilocarpusjaborandi Pilocarpine, Glaucoma

(Fam-Rutaceae) Pilosine

8.Steroidal alkaloids
1 Ashwagandha Root and stem bases ofWithania Withanine, Sedative,
Somnifera Somniferine, Anti rheumatic
(Fam-Solanaceae) Withanolide(ste
roid)
2 Kurchi Stem bark of Holarrhena Conessine, Antiamoebic
Antidysenterica Isoconessine
(Fam-Apocyanaceae)
3 Veratrum Root and Rhizome of Germidine, Hypotensive,
Veratrum Viride ,Veratrum Album Protoveratrine Cardiac
Fam-Liliaceae A&B depressant
9.Quinazoline alkaloids
1 Vasaka Leaves of Adhatoda vasica Vasicine, Antitussives,
(Fam-Acanthaceae) Vasicinone Expectorant

Non-heterocyclic alkaloids

1.Diterpenealkaloids

Sl Name Biological source Active Uses

no constituents
1 Aconite Dried roots of Aconitum napellus, Aconite, Anti rhuematic
(Fam-Ranunculaceae) neopelline
2. Amino alkaloids
1 Colchicum Ripe seed of Colchicum Luteum or Colchicine, Gout
(meadow C. Automnale demecolcine Induction of
saffron seed) (Fam-Liliaceae) polyploidy

2 Ephedra Stem of Ephedra Gerardiana Ephedrine, Antiasthmatic,

Or E. Nebrodensis pseudo Hay fever
(Fam- Gnetaceae or Ephedraceae) Ephedrine
3 Gloriosa Dried rhizomes and roots of Gloriosa Colchicine Gout
–superba Anti cancer
(Fam-liiaceae)

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Alkaloids

Miscellaneousalkaloids
1 Bhringraj Entire herb Eciliptica –alba Wedilolactone Brain tonic
(Fam-Asteraceae) Ecliptine Hepato
protective
2 Punarnava Dried herb Boerhaavia diffuse Punernavoside, Jaundice,
(Fam-Nictginaceae) boervinone Diuretic
3 Shankupushpi Aerial parts of Canscoradecussate Bitter Nervous
(Fam-Gentianaceae) substances, debility
triterpenes

ALKALOIDS
DERIVED FROM

NICOTINIC
ORNITHINE TYROSINE TRYPTOPHAN ACID LYSINE

1)Indole
1)Pyrrolidine 1)Iso-quinoline 1)Piperidine
2)Quinoline
2)Tropane 2)Phenylethylamine 1)Pyridine 2)Quinolizidine
3)Pyrrolizidine 3)Indolizidine

NOTES ON INDIVIDUAL DRUGS

ORNITHINE DERIVED ALKALOIDS

1)TROPANE ALKALOIDS:Obtained by the condensation of one mole each of pyrrolidine and

piperidine

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Alkaloids

 Bicyclic system made up of a 5-membered ring (1, N, 5, 6, and 7) and a

6-membered ring (1, 2, 3, 4, 5, N). N is commonto both. The nucleus
always carries oxygen in position 3.
 The nitrogen is always methylated. The oxygen is substituted with an
aromatic acid, therefore, creating an ester.

1) Atropine 2) Hyoscyamine 3) Hyoscine

 Hyoscyamine is the pure optical isomer; (+)Hyoscyamine, (–) Hyoscyamine.

Atropine is the racemic ofHyoscyamine.
 Atropine = (±) Hyoscyamine
 The 3-hydroxy derivative of Tropane is known as TROPINE.

 Esterification of tropine with tropic acid yields Hyoscyamine

 Epoxy derivative of hyoscyamine in hyoscine

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Alkaloids

 Eg:Belladona,Datura,Hyoscyamus,Stramonium,coca,Duboisia
 Therapeutic value is present only in hyoscine,hyoscyamine and racemic form of
hyoscyamine ie,Atropine

BELLADONNA HERB(Syllabus)

Biological Source:Dried leaves and flowering tops of Atropa belladonna or Atropa acuminate
(Fam: Solanacea)

Microscopic characters

 Epidermis – Slightly wavy anticlinal wall and striated cuticle, Anisocytic stomata or
(cruciferous) but also Anomocytic stomata (Less in number)
 Trichomes – Glandular trichomes– Uniseriate and unicellular heads, occasionally
uniserate and multicellular
 Palisade ratio – 5 to 7
 Mesophyll – Sandy or microsphenoidal crystal of calcium oxalate

Macroscopic characters
 Leaves are Ovate-lanceolate to broadly ovate
 Entire margin, acuminate apex
 Leaves – Green to brownish green
 Flowers- Purple to yellowish brown
 Taste –Bitter

Chemical constituents
 Total alkaloidal content of drug is 0.4 to 1%
 Major alkaloids :l –hyoscyamine & atropine
 Also contains belladonine,hyoscine,pyridine, N-methyl pyrroline and scopoletin-a
fluorescent substance
Uses
 Anticholinergic drug-Used to reduce secretions such as sweat ,saliva and gastric juice
 As antispasmodic agent
 As an antidote in opium and chloral hydrate poisoning

Adulterants and substitutes

1.Phytolacca Americana or P. Decandra
 Idioblast present, Needle (Acicular type crystal), Anomocytic stomata
2. Solanum Nigrum
 Palisade ratio 2–4
3. Alianthus Glandulosa

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Alkaloids

 Cluster crystal of calcium oxalate, unicellular lignified trichomes,straight walled

epidermal cell showing striated cuticle

DATURA

Biological source: Dried leaves and flowering tops of Datura metel of fam.Solaneceae

Microscopic characters
 Stomata –Anisocytic or cruciferous
 Cells covered with thin cuticle and glandular and non-glandular trichomes
 Spongy parenchyma contains calcium oxalate crystals

Macroscopic characters
 Unpleasant odour and bitter taste
 Leaf unequal at the base with acute apex
 Flowers are funnel shaped
 Brown coloured seeds are triangular and found in thorny capsule

Chemical constituents
 Major alkaloid - Hyoscine (scopolamine)
 Minor alkaloid - Atropine &l-hyoscyamine
Uses
 Used in cerebral excitement
 Along with morphine ,it is used as preoperative medication
 Treatment of cough and asthma
 Hyoscine hydrobromide is used in motion sickness, gastric or duodenal ulcers

Chemical test

1. Vitali-Morin reaction

Tropane alkaloid +fuming nitric acid

Evaporated to dryness + methanolic potassium hydroxide

Violet colour

2. Hyoscine hydrobromide solution + silver nitrate solution

SAMSON’S MEDLIN 10
Alkaloids

Yellowish white ppt

(Insoluble in nitric acid, soluble in dil.ammonia)

HYOSCYAMUS

Biological source : Dried leaves and flowering tops of Hyoscyamus niger of fam.Solanaceae

Microscopic characters

 Leaf is dorsiventral
 Epidermis: Smooth cuticle &glandular trichomes
 Stomata: Anisocytic
 Spongy mesophyll contain prismatic calcium oxalate crystals
 Near the veins, some times idioblasts are present containing microsphenoidal crystals

Chemical constituents

 Principal alkaloid: Hyoscyamine

 Atropine and hyoscine are present in fewer amount
Uses

 Relieve spasm of urinary tract

 Sedative
 Used to check salivary secretions
 Expectorant, antispasmodic and antiasthmatic

STRAMONIUM

Biological source:Dried leaves and flowering tops of Datura stramonium of fam.Solanaceae.

Microscopic characters

 Wavy epidermal cells

 Palisade tissue contain calcium oxalate prisms
 Epidermis shows numerous uniseriate covering trichomes and occasionally short
glandular trichomes are present
 Stomata- Anisocytic
Chemical constituents

 Major alkaloid : l-hyosciamine and hyoscine

 Minor alkaloid : Atropine

SAMSON’S MEDLIN 11
Alkaloids

Uses

 Used to control salivation, muscular rigidity and tremors in parkinsonism

 Motion sickness
 Treatment of asthma

COCA LEAVES

Biological source: Dried leaves ofErythroxylon coca and Erythroxylon truxillense of fam.
Erythroxylaceae

Microscopic characters

 Lower epidermis shows papillae and numerous Paracytic stomata

 Palisade parenchyma contains prismatic calcium oxalate crystals
 Lignified Idioblast near vein
Chemical constituent

 Cocaine,cinnamyl cocaine,α truxilline,tropocaine,benzoyltropine,dihydroxytropane and

benzoylecgonine
 The price of leaves is determined on the basis of ecgonine content,because it is
converted synthetically in to commercial cocaine
 Cinnamyl cocaine ecgonine + methyl alcohol + cinnamic acid
 Cocaine ecgonine + methyl alcohol +benzoic acid
 α truxilline ecgonine + methyl alcohol + αtruxillic acid
Chemical test

Cocaine powder + H2SO4 + H2O Characteristic smell of methyl benzoate

Uses : Local anaesthetic

DUBOISIA

Biological source: Dried leaves of Duboisia myoporoides and Duboisia leichhardtii of fam.
Solanaceae

Macroscopic characters

 Leaves: Tapering at both ends and alternatively arranged

 Colour: Pale green
 Taste : Intensely bitter

SAMSON’S MEDLIN 12
Alkaloids

Chemical constituents

 Scopalamine and atropine

 l-hyoscyaminewhich is converted to atropine during extraction

Uses

 Anticholinergic drug
 As antidote for pilocarpine,physostigmine and other choline esters
 Relieves bronchial spasm in asthma
 In peptic ulcer
Chemical tests

1) Addition of gold chloride solution to atropine in water and hydrochloric acid gives
yellow precipitate
2) Give positive vitali Morin reaction

TYROSINE DERIVED ALKALOID

A) ISO-QUINOLINE ALKALOIDS
 Examples are :Opium, Ipecac , Curare

OPIUM(syllabus)

Biological source:Opium is the latex obtained by incision from the unripe capsules of Papaver
somniferum (Papaveracea)

Production:Sowing takes place in November and collection from April to June. The incisions
are made in the afternoon with an instrument known as a 'nushtur.The latex, which is at first
white, rapidly coagulates and turns brown. Early in the morning of the day following the making
of the incisions the partly dried latex is scraped off with a trowel-like 'seetooar'. Each capsule is
cut several times at intervals of 2 or 3 days. After collection the latex is placed in a tilted vessel
so that the dark fluid (pussewah) which is not required may drain off. By exposure to air the
opium acquiresa suitable consistency for packing.

Microscopy
 Agglomerated latex granules in irregular masses
 Pointed trichomes and a few starch grains may be present

Chemical constituents
 Opium alkaloids are present as salt of meconic acid
 Benzylisoquinoline type:Narcotine (noscapine)

SAMSON’S MEDLIN 13
Alkaloids

Narceine
Papaverine

 Phenanthrene type : Morphine

Codeine
Thebaine
 Morphine –monoacidic,laevorotatory,phenolic alkaloids
 Diacetyl derivative of morphine is heroin
 Codeine-monoacidic base,laevorotatory
 Papaverine-monoacidic base,laevorotatory,optically inactive
 Also contains sugar ,mucilage and salts of calcium,potassium and magnesium

Chemical test
 Opium dissolved in water + ferric chloride solution Deep reddish purple colour
(due to presence of meconic acid)
 Morphine + nitric acid Orange red colour
 Morphine + potassium ferricyanide and ferric chloride Bluish green colour
 Papaverine solution in HCL + potassium ferricyanide Lemon yellow colour

Uses
 Analgesic
 Sedatives & hypnotics
 Morphine produces respiratory depression & constipation
 Codeine-As an antitussive in cough preparations
 Papaverine-smooth muscle relaxant
 Morphine +2(COCH3) Heroin : more potent narcotic & analgesic than morphine
 Morphine ,by losing one molecule of water gives apomorphine which is emetic and used
to treat poisoining cases

IPECACUANHA

Biological source: Dried roots or rhizome and root of Cephaelis ipecacuanha or Cephaelis
acuminata, belonging to fam Rubiaceae

Microscopy
 Cork-Polygonal cells with granular brown matter.
 Parenchyma-Thin walled polyhedral cells with starch grains& calcium oxalate crystals
 Xylem-Tracheids and small vessels

Chemical constituents
 Phenolic : Cephaeline and psychotrine
 Non Phenolic : Emetine , psychotrine methyl ether
 Cephaeline is converted to emetine by methylation of phenolic C (6)
hydroxyl group

SAMSON’S MEDLIN 14
Alkaloids

Chemical test
 Ipecac +HCL +water filter Filtrate +potassium chlorate
yellow colour changes to red (due to emetine)

 Emetine +H2SO4 +Sodium molybdate (Frohde’s reagent)Bright green colour

Uses
 Expectorant
 Anti protozoal
 Emetic

CURARE

Biological source:Dried extract of stem and leaves ofChondrodendron tomentosum of fam

Loganiaceae & Menispermaceae

Chemical constituents
 (+)tubocurarine, curine, curarine, isochondrodendrin, cycleanine,chondrocurine,
tomentocurine etc

Chemical test
 Drug + ferric chloride Green colour
 Drug + mercuric nitrate solution Cherry red colour
Uses
 As a skeletal muscle relaxant due to neuromuscular blocking actions
 Diagnosis of myasthenia gravis

B)PHENYLETHYLAMINE ALKALOID

EPHEDRA(syllabus)

Biological source:Dried young stems of ephedra gerardiana and E.nebrodensis of fam

Gnetaceae

Microscopic characters
 Epidermis – Unicellular quadrangular cells with thick cuticle, sunken stomata and
papillae on the ridges
 Cortex-Chlorenchymatous,Thin walled cellulosic Parenchyma, Calcium oxalate crystals
are present
 Lignified Pericycle fibers, Brownish matter in pith

Chemical constituents
 Ephedra contains amino alkaloids.They are ephedrine,nor-ephedrine, n-methyl ephedrine,
pseudo- ephedrine etc
SAMSON’S MEDLIN 15
Alkaloids

Chemical test
Epedrine dissolved in water & dil. HCL, then treated with copper sulphate and NaOH
gives violet colour and if shaken with solvent ether, the organic layer shows purple and aqueous
layer shows blue colour

Uses
 Sympathomimetic drug
 In asthma as bronchodilator
 In the treatment of hay fever & hypertension

TRYPTOPHAN DERIVED ALKALOIDS

A)INDOLE ALKALOIDS

Examples: Nuxvomica,Ergot,Rauwolfia,Vinca, Physostigma

NUXVOMICA

Biological source :Dried, ripe seeds of Strychnos nux-vomica of fam.Loganiacea

Macroscopic characters
 Seeds are disc shaped , flat or irregularly bent and concavo-convex
 The testa is covered with silky, closely appressed radiating hairs
 In the centre ofone ofthe f'lattened sides is a distinct hilum, and a small prominence on
the circumference marks theposition of the micropyle
 Hilum and micropyle are joined by a radial ridge
 Small embryo with two cordate cotyledons and a cylindrical radicle

Microscopic characters
 Epidermis :Lignified unicellular covering trichomes
 Collapsed cell layer in seed coat
 Endosperm is made up of polyhedral unlignified cells with plasmodesmata
 Aleurone grainand Oil globules
 Calcium oxalate crystals and starch grains are absent

Chemical constituents
 Chief constituents :strychnine, brucine
 Strychnine is more physiologically active than brucine
 Bark contains brucine and traces of strychnine
 Wood and root of plant contains strychnine
 α-colubrine, isostrychnine,protostrychnine, pseudo strychnine,novacine and strychnicine
are also present
 Contain glycosides like, loganin,chlorogenic acid and fixed oi
Uses
SAMSON’S MEDLIN 16
Alkaloids

 Cardiac and respiratory stimulant

 Bitter stomachic and tonic
 Brucine used for denaturing alcohol and inedible fats
 As dog poison

Chemical tests
 Strychnine+ ammonium vanadate +H2SO4 Purple colour

 Brucine+ con.nitric acid yellow colour

 Srychnine + H2SO4 + potassium dichromate violet colour

Adulterants
 Dried seeds of strychnos nuxblenda:Regular in shape & traces of alkaloids
 Dried seeds of strychnos potatorum:Smaller and thicker with yellowish buff colour

RAUWOLFIA(Syllabus)

Biological source:Dried rhizome and roots of Rauwolfia serpentina of fam . Apocynacea

Macroscopical characters
 Rhizome closely resemble the root but may be identified by a small central pith
 The drug breaks readily with a short fracture
 Both bark and wood contain abundant starch

Microscopy
 Cork- Stratified cells
 Phelloderm-10–12 rows of parenchymatous cells. Few cells contains starch grains and
few latex cells
 Secondary phloem (Non lignified)-Sieve tube, Companion cells, Phloem parenchyma
with starch grain and calcium oxalate crystal.
 Xylem:Extensively lignified
 Stone cells and phloem fibres are absent

Chemical constituents
 Alkaloids are concentrated mainly in the bark of roots
 More than 30 alkaloids are present
 Important alkaloid- reserpine
 Other alkaloids are ajmaline,ajmalicine,rescinnamine,reserpinine,yohimbine,serpentine &
serpentinine
 Apart from alkaloids,contains oleo resins,phytosterol,fatty acids,alcohol and sugars

Cultivation
 It grows mainly in humid conditions and in clay loamy soil with large amount of humus
 Good drainage are supposed to be ideal
 PH of soil should be acidic and around 4 and temperature for cultivation is 100 -380
SAMSON’S MEDLIN 17
Alkaloids

 Soil containing large amount of sand make plant more susceptible to diseases
 Propagated mainly by seeds.Seedlings are then transplanted in the month of august at a
distance of 16 to 30 cm.
 Uprooted when plants are about 3 to 4 yrs old
 Roots are cut properly ,washed so as to remove earthy matter and dried in air

Chemical tests
 Drug +con. Nitric acid Red colour along the medullary rays
 Reserpine + vanillin in acetic acid Violet red colour
 Powdered drug + H2SO4 +P-di-methyl amino benzaldehyde violet to red colour

Uses
 Antihypertensive
 Neuropsychiatric disorder
 Ajmalicine- Treatment of circulatory disease

VINCA (Syllabus)

Biological source :Dried whole plant of Catharanthus roseus of fam .Apocynaceae

Microscopic characters

 Stomata-Cruciferous
 Epidermal cells-Covering trichomes
 Midrib-Presence of collenchyma
 Spongy parenchyma

Chemical constituents
 Major alkaloid- Vincristine,vinblastine
 Other alkaloids:vindoline,ajmalicine,lochnerine,serpentine & tetrahydroalstonine

Uses
 Anti neoplastic
 Hodkings disease
 Acute lymphocytic lukemia
 Anti diabetic

ERGOT

Biological source:Dried sclerotium of a fungus,Claviceps purpurea (Clavicipitaceae or

hypocraceae) developed in the ovary of rye plant Secale cereale of fam .Graminae

Life cycle of ergot

SAMSON’S MEDLIN 18
Alkaloids

Sphacelial stage

The ovary of rye, the plant get infected by the ascospore of the fungus

(Carried by the wind / insects to the

base of young ovary)

Spore germinate, forming filamentous hyphae which enter the ovary by enzyme action

Form a soft, white mass (Mycelium)

Secrets a viscous and sugary fluid called honey dew

 During the sphacelias stage the hyphae only penetratethe outer part of the ovary

Sclerotium stage

 Hyphae penetrate deeper parts of the ovary &replace the entire mass of ovary with a
compact tissuecalled pseudoparenchyma known as sclerotium stage
 This stage is considered as the resting or dormant stage of fungus
 Consists maximum amount of ergot alkaloids

Ascospore stage
 Sclerotium that are not collected fall on the ground and form stroma ,which are
elongated form
 Each stromatum has a globular head and a stalk
 Head portion contains large number of perithecia
 Each perithecia contains a number of sac ,each sac containing Ascospores
 Ascospores are sexual spores capable of inducing fresh life cycle of fungus by infecting
ovary of rye plant

Microscopy
Sclerotium
 outer layer: flattened polygonal cells, Purple to dark brown colour
 Inner layer: dense Pseudo Parenchymatous cells composed of Chitin
 Central region(mycelia cells) - Consists of round/oval with high refractive walls,contain
fixed oils

Chemical constituents

 Divided into two classes: (1) Clavinetype alkaloids

(2) Lysergic acid derivatives (peptide alkaloids)

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Alkaloids

 Lysergic acid derivative contains the pharmacologically active alkaloids

 Six pairs of alkaloids predominate in the sclerotium and fall into eitherthe water-soluble
ergometrine (or ergonovine) group or the water-insoluble ergotamine and 'ergotoxine'
group

 Levoform is medicinally active while dextro form is inert in action

l. Ergometrine group 2.Ergotamine group 3 Ergotoxine group

Ergometrine (levo) Ergotamine Ergocristine

Ergometrinine (dextro) Ergotaminine Ergocristinine
Ergosine Ergocryptine
Ergosinine Ergocryptinine
Ergocornine
Ergocorninine
Chemical tests

 Van –Urk’s test

Ergot + p-dimethylaminobenzaldehyde Blue colour

 Ergometrine + water Blue fluorescence

 Ergot + solvent ether + H2SO4 filterFiltrate + sod.bicarbonate Violet colour
in aq.layer
 Ergotamine + glacial acetic acid +ethyl acetate

A small portion of soln +H2SO4

Blue colour with red tinge appear

Ferric chloride

Blue colour appear while red tinge become faint

Uses
 Ergometrine – used as oxytocic
 Ergotamine – As analgesic in treatment of migraine
 Ergotoxine methanesulphonates – used in geriatric patients for treatment of dementia
 LSD- semisynthetic derivative ,used in psychiatry

PHYSOSTIGMA

Biological source : Dried ripe seeds of physostigma venenosum of fam.Leguminosae

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Alkaloids

Chemical constituents

 Major alkaloid :Physostigmine

 Minor alkaloid: Eseramine , geneserine, physovenine, calabatine ,calabasine
Isophysostigmine and N-8- norphysostigmine
 It is to be preserved properly from air and light as it is oxidized in to rubeserine
, a red colour compound

Uses
 Parasympathomimetic drug
 To contract pupil of eye
 Antidote of tricyclic antidepressants

2)QUINOLINE ALKALOIDS :Examples - Camptotheca , cinchona

CAMPTOTHECA

Biological source:Dried stem wood of camptotheca acuminateand camptotheca lowreyona of

fam.Nyssaceae

Chemical constituents
 Major alkaloid : Camptothecin
 Minor alkaloids : Irinotecan, topotecan, 9-aminocamptothecin,10- hydroxycamptothecin
and 10-methoxy camptothecin
 Young leaves contains higher concentration of camptothecin
 It doesn’t respond to Dragendorff’s and mayer’s reagent

Uses
 Prototype DNA topoisomerase 1 inhibitor
 Antitumor activity

CINCHONA(Syllabus)

Biological source: Dried bark of Cinchona calisaya,C.ledgeriana,C.officinalis,C.succirubra of

fam . Rubiaceae

Macroscopy

Stem bark Root bark

Shape Curved, Quill & transverse fissures Curved, twisted or irregularly channelled
outer surface Grey colour, rough, Exfoliation in some Reddish brown Scaly
Case
Inner surface Striated and yellowish to deep reddish Striated and Reddish brown
Brown
Fracture Short in outer bark and fibrous in inner Fibrous
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Alkaloids

Part

Microscopy
 Cork –phelloderm:Flat polygonal cells with reddish brown matter
 Idioblast of calcium oxalate is the specific characteristic of cinchona bark
 Parenchymatous tissues :Starch grains present
 Stone cell absent

Chemical constituents
 The principal alkaloids are the stereoisomersquinine and quinidine and their
respective6’ demethoxy derivatives,cinchonidine andcinchonine
 The alkaloids appear to be present in combination with quinic acid and cinchotannic
acidand a glycoside quinovintannins and bitter essential oil
 Quinidine is also obtained commercially from cuprea bark
 Quinine shows a strong blue fluorescence in UV light

Chemical test
 Dry powder + glacial acetic acid heatPurple vapours are formed
 Thallequin test : Powdered drug +bromine H2o +dil ammonia Emrald green
colour
 Quinidine +silver nitrate soln white ppt

Uses
 Quinine : Antimalarial ,protoplasmic poison
 Quinidine :Prevention of atrial fibrillation ,cardiac depressants

NICOTINIC ACID DERIVATIVES

PYRIDINE ALKALOIDS :Examples are Arecanut and Lobelia

1)ARECA NUT

Biological source :Dried ripe seeds of Areca catechu of fam.Palmae

Chemical Constituents
 Arecoline,arecaidine,guvacine and guvacoline
 Also contains lipids,volatile oil,tannins and gums
 Only arecoline possess physiological activity

Uses
 Parasympathomimetic drug& Areca has sialogogue properties
 Anthelmentic and used as vermicide & taenifuge in veterinary practice. Not used in
human medicine
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Alkaloids

2)TOBACO

Biological source: Dried leaves of Nicotiana tobacum , of fam. Solanaceae

Chemical constituents
 Contains pyridine – Piperidine type of alkaloids
 Major alkaloid: Nicotine
 Minor alkaloids : Nornicotine & Anabasine

Uses

 Used as insecticides
 Stimulant effects on heart and nervous system

LYSINE DERIVED ALKALOIDS

1)PIPERIDINE ALKALOIDS

1)PEPPER

Biological source:Dried, unripe fiuits of Piper nigrum of fam .Piperacea

Chemical constituents
 Pepper contain s l-2.5% of volatile oil, 5-9% of the crystalline alkaloids piperine and
piperettine, and a resin.
 The aroma of the spice is due to the volatile oil. which consists largely ofterpenes
 The pungency is ascribed to piperine and the resin

Use
 Chronic bronchitis
 It is used as an insecticide.
 Employed extensively as condiment in food preparations

2)LOBELIA

Biological source : Dried aerial parts of lobelia nicotianaefolia of fam. Campanulaceae

Chemical constituents

 Lobeline,lobelidine,lobelanine,isolobelanine and lobelanidine

 Also contsains pungent volatile oil,resins ,gum and fixed oil

Chemical test

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Alkaloids

 Lobeline+ sulphuric acid red colour with formaldehyde

 Lobeline solution on boiling produces acetophenone which is recognised by smell

Uses

 Used in asthma as respiratory stimulant

 As smoking deterrent
 As cardiovascular stimulant

ALKALOIDS DERIVED FROM HISTIDINE

IMIDAZOLE ALKALOIDS

PILOCARPUS

Biological source: Pilocarpine is obtained from the leaves of closely related plants of the
genusPilocarpus, belonging to fam . Rutaceae.
However, the genus comprised of a variety of species commonly known by various names, such
as: Pilocarpus jaborandi (Pernambuco Jaborandi),(Pilocarpus pennatifolius (Paraguay
Jaborandi); Pilocarpus microphyllus (Maranham Jaborandi); Pilocarpus selloanus (Rio
Jaborandi); Pilocarpus trachylophus (Ceara Jaborandi); Pilocarpusspicatus (Aracati
Jaborandi); Pilocarpus heterophyllus (Barqui Simento Jaborandi); and Pilocarpus racemosus
(Guadeloupe).

Chemical constituents

 Pilocarpine
 Isopilocarpine, pilocarpidine, pilosine, psuedopilocarpine, isopilosine
 The oil cells observed in the leaf gives volatile oil containing different monoterpenes like
limonene,α- pinene,sabinene and sesquiterpenes
Uses

 In ophthalmology for the treatment of Glaucoma

STEROIDAL ALKALOIDS :Examples – Ashwagandha, Kurchi

1)ASHWAGANDHA

Biological source: Dried root and stem bases of Withania somnifera of fam .Solanaceae

Chemical constituents

 Main constituents are alkaloids and steroidal lactones

 Among various alkaloids ,withanine is the main constituent

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Alkaloids

 Other alkaloids are somniferine, somnine, somniferinine, withananine, pseudo-withanine,

tropine,3-α-gloyloxytropane,choline,cuscohygrine,isopelletierine,anaferine &anahydrine
 Two acyl steryl glucosides : Sitoindoside VII , sitoindoside VIII
 Leaves contain steroidal lactones called Withanolides like withaferin and withanolide

Uses

 Sedative & hypnotic

 Immuno-modulatory agent
 Treatment of rheumatism,gout
 Sex stimulant and rejuvenator

2)KURCHI

Biological source: Dried stem bark of Holarrhena antidysentrica of fam. Apocynaceae

Microscopic characters

 Cork:Tangentially and radially elongated cells , stone cells are present

 Phloem :Contain sieve tubes, companion cells ,phloem parenchyma & stone cells
 Prismatic calcium oxalate crystals (Rhombohedral ) are present

Chemical constituents

 Conessine, norconessine, isoconessine, dioxyconessine, conessimine, holarrhimine &

holarrhidine
Uses

 Antiprotozoal

AMINO ALKALOIDS (PROTO-ALKALOIDS)

1)COLCHICUM

Biological source: Dried ripe seeds of Colchicum luteum and Colchium autumnale of fam
.Liliaceae

Microscopic characters

 Parenchymatous cells are reddish brown with thick walls

 Endospermic cells show pitted walls , aleurone grains and fixed oil
 Xylem vessels are spiral or annular

Chemical constituents

 Contain 0.2- 1 percent of amino alkaloids

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Alkaloids

 Colchicine is the major constituent & demecolcine

Chemical tests

 Colchicine + sulphuric acid Yellow colour

 Alcoholic solution of colchicine + ferric chloride Red colour

Uses

 Treatment of gout and rheumatism

 Antitumour activity
 Used in horticulture
 Induce polyploidy

2)GLORIOSA

Biological source : Dried rhizomes & roots of Gloriosa superba of fam . Liliaceae

Chemical constituents
 Colchicine
Uses
 Treatment of gout and inflammation

PURINE ALKALOIDS

o This group of alkaloids mainly include caffeine, theobromine and theophylline

o Contain purine base which is a fusion of an imidazole ring pyrimidine ring
o Examples – Cocoa, Kola,Coffee,Tea

1)COCOA

Biological source:Obtained from the seeds of Theobroma cocoa of fam. Sterculiaceae

Chemical constituents

 Theobromine and cocoa butter

 Less percentage of caffeine, polyphenols etc.

Uses
 Theobromine -Stimulant & diuretic properties
 Cocao butter -As nutritive & suppository base in pharmaceuticals

2)COFFEE HERB

Biological source: Dried ripe seeds of Coffea arabica or Coffea liberica of fam. Rubiaceae

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Alkaloids

Chemical constituents

 Caffeine, tannin,fixed oils and proteins

 During roasting process ,agreeable smell of coffee is developed due to oil called Caffeol
 Chlorogenic or caffeotannic acid and sugars

Uses
 As a source of caffeine
 Stimulant and diuretic properties

DITERPENE ALKALOIDS: Example- Aconite

ACONITE

Biological source : Dried root of Aconitum napellusm of fam.Ranunculaceae

Chemical constituents

 Aconitine , hypoaconitine,neopelline, napelline, neoline

 Traces of sparteine and ephedrine
 Also contains aconitic acid,succinic acid and starch

Aconitine HydrolysisBenzoyl aconine + Acetic acid

Benzoyl aconine Hydrolysis Aconine + Benzoic acid

 The products of hydrolysis are less active

Uses
 Highly poisonous drug
 Treatment of neuralgia , sciatica, rheumatism and inflammation
 Analgesic and cardiac depressant

QUINAZOLINE ALKALOIDS

VASAKA

Biological source:Dried as well as fresh leaves of plant Adhatoda vasica of fam. Acanthaceae

Microscopic characters
 Epidermis:Caryophyllaceous(or Diacytic) stomata with sinuous epidermal cells
 Covering and glandular trichomes
 Midrib:Bicollateralvascular bundles are seen
 Mesophyll :Contains prismatic and acicular crystals of calcium oxalate

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Alkaloids

Chemical constituents
 Vasicine,vasicinone and 6-hydroxy vasicine
 Vasicine is oxidised to vasicinone,which is a bronchodilator
 Also contains volatile oil ,betain and vasakin and adhatodic acid

Uses
 Expectorant and bronchodilator
 Vasicine shows oxytocic & abortificient action
 Bromhexine is a synthetic derivative of vasicine ,which reduces the viscocity of sputum

SPECIFIC TESTS FOR ALKALOIDS

Alkaloids Test Colour

Van-urk’s Test
Ergot Alkaloids Para dimethyl Blue colour
aminobenzaldehyde
Purple colour upon
Murexide Test exposure to ammonia
Purine Alkaloids KClO3 + HCl — Heat solution. This colour
disappears upon addition
of alkali.
Vitali – Morin Reaction
Fuming HNO3+ dry to get
Tropane Alkaloids residue + add Methanolic Violet colour
potassium hydroxide to an
acetone solution of nitrated
residue
Meconic Acid Test
Opium Alkaloids FeCl3 + Dil. HCl Reddish purple colour
Thalleoquin Test
Cinchona Alkaloids Bromine water + Dil. Ammonia Green colour
solution

Stomata type of different alkaloids

Stomata type Examples

Anomocytic/ Ranunculaceous/ Lobelia
Irregular Celled Stomata
Diacytic/
Caryophyllaceous/Cross-Celled Vasaka

SAMSON’S MEDLIN 28
Alkaloids

Stomata
Anisocytic/Cruciferous/Unequal Balladonna,Datura,
Celled Stomata Vinca
Paracytic/Rubiaceous/Parallel
Celled Stomata Coca

Alkaloidal Class Synthesis Steps Examples

Isoquinoline Tyrosine or Phenylalanine → Papaverine,Narcotine, Emetine,
Derivatives Dopamine or Tyramine Morphine,Codeine,Thebaine

Quinoline Derivatives Tryptophan → Tryptamine → Quinine, Quinidine, Cinchonine,

Strictosidine (with Secologanin) Cinhonidine
→Korinanteal → Cinhoninon
Indole Derivatives Tryptophan → Tryptamineor
5-Hydroxy Triptophan
Psilocybin,Physostigmine,Physovenine
Tryptophan → Chanoclavine Ergotamine, Ergosine, Ajmalicine,
→ Agroclavine → Elimoclavine Sarpagine, Ajmaline, Yohimbine,
→ Reserpine, Strychnine,Brucine
Paspalic acid → Lysergic Acid

Tryptophan → Tryptamine →
Strictosidine
(with Secologanin)

Imidazole Derivatives Directly from Histidine Pilocarpine, Pilosine

Purine Derivatives Xantosine → 7-MethylXantone Caffeine , Theobromine, Theophylline

→ 7-Methyl Xanthine →
Theobromine → Caffeine

Beta Phenylethyl Tyrosine or phenylalanine Ephedrine,Pseudoephedrine,Mescaline,

Amine → Dioxyphenilalanine → Catecholamine’s (Adrenaline, Nor
Derivatives Dopamine → Adrenaline and adrenaline,Dopamine)
Mescaline,Tyrosine or
Phenylalanine→ 1Phenylpropane-
1, 2-dione → Cathinone →
Ephedrine andPseudoephedrine
Tropolene Derivatives Tyrosine or phenylalanine Colchicine

SAMSON’S MEDLIN 29
Alkaloids

→ Dopamine → Autumnaline
→ Colchicine
Diterpene Derivatives Mevalonic acid → Isopentenyl Aconitine
Pyrophosphate → Geranyl
Pyrophosphate
Steroid Derivatives Cholesterol, Arginine Solasodine, Solanidine

SAMSON’S MEDLIN 30